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Shortly after starting a new job last year, I won a non-specific vacation of my choosing to the tune of a few thousand dollars as a taxable benefit. Now that the pandemic has sort of shut down global leisure travel and the future is hazy, I'd like to ask the CEO if it's possible to exchange the vacation for some other token gift, like some fancy devices that may be useful for work or entertainment in the near-term.

It's been communicated to me that the prize is somewhat vague and not restricted by time, but this discussion was long before any part of life was interrupted. The question is, is there any reason the specific type of gift would be important and non-arbitrary, or would there be a good reason they'd decline this request?

For further context, this is in Canada, and no specific trip has been purchased. This would come in the form of my purchases up to a certain amount being reimbursed later.

  • You can always ask. Just be prepared to hear an answer of "No". – Joel Etherton Apr 21 at 21:54
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It's certainly possible that the company wouldn't be able to exchange the gift for something else. It's possible that they already purchased the prize and can't realistically get a refund. It is also possible, particularly if the company does a lot of business travel, that the company's travel vendor gave them the prize and they chose to use it as a prize rather than using it to pay for a subsequent business trip.

There is likely no harm in asking to see if the prize can be exchanged-- the point of the prize, after all, was to reward employees. Of course, if your company is actively laying people off and/or clearly hemorrhaging cash as a result of COVID-19, you may want to wait for things to settle down before you approach the CEO about exchanging a gift.

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    Those are definitely some aspects I hadn't considered. Edited for further context. – chazbono Apr 21 at 21:26

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